Quantitative structure-activity relationship analysis of perfluoroiso-propyldinitrobenzene derivatives known as photosystem II electron transfer inhibitors

Mehmet Sayim Karacan, Çiǧdem Yakan, Mehmet Yakan, Nurcan Karacan, Sergey K. Zharmukhamedov, Alexandr Shitov, Dmitry A. Los, Vyacheslav V. Klimov, Suleyman I. Allakhverdiev

    Research output: Contribution to journalArticlepeer-review

    16 Citations (Scopus)

    Abstract

    Quantitative structure-activity relationship (QSAR) analysis of the twenty-six perfluoroisopropyl-dinitrobenzene (PFIPDNB) derivatives was performed to explain their ability to suppress photochemical activity of the plants photosystem II using chloroplasts and subchloroplast thylakoid membranes enriched in photosystem II, called DT-20. Compounds were optimized by semi-empirical PM3 and DFT/B3LYP/6-31G methods. The Heuristic and the Best Multi-Linear Regression (BMLR) method in CODESSA were used to select the most appropriate molecular descriptors and to develop a linear QSAR model between experimental pI50 values and the most significant set of the descriptors. The obtained models were validated by cross-validation (R 2cv) and internal validation to confirm the stability and good predictive ability. The obtained eight models with five-parameter show that: (a) coefficient (R2) value of the chloroplast samples are slightly higher than that of the DT-20 samples both of Heuristic and BMLR models; (b) the coefficients of the BMLR models are slightly higher than that of Heuristic models both of chloroplasts and DT-20 samples; (c) The YZ shadow parameter and the indicator parameter, for presence of NO2 substituent in the ring, are the most important descriptor at PM3-based and DFT-based QSAR models, respectively. This article is part of a Special Issue entitled: Photosynthesis Research for Sustainability: from Natural to Artificial.

    Original languageEnglish
    Pages (from-to)1229-1236
    Number of pages8
    JournalBiochimica et Biophysica Acta - Bioenergetics
    Volume1817
    Issue number8
    DOIs
    Publication statusPublished - Aug 2012

    Keywords

    • CODESSA
    • Perfluoroisopropyldinitrobenzene derivatives
    • Photosynthetic inhibitory activity
    • Photosystem II
    • QSAR

    ASJC Scopus subject areas

    • Biophysics
    • Biochemistry
    • Cell Biology

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